


Unexpected

by spiralicious



Category: Supernatural
Genre: Community: allbingo, Crossdressing, F/M, Late Night Conversations, Winterfest in July Bingo 2019
Language: English
Status: Completed
Published: 2019-08-01
Updated: 2019-08-01
Packaged: 2020-07-28 16:36:07
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 770
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20067163
Author URL: https://archiveofourown.org/users/spiralicious/pseuds/spiralicious
Summary: Rowena doesn't know why Sam has shown up at her door in the middle of the night in a dress, but she's keen to find out.





	Unexpected

“Oh dear lord, who dressed you?” Rowena stared at the tottering Sam Winchester, who had unexpectedly shown up at her door. He ducked his head shyly, tucking some hair behind his ear. She noticed his unsteadiness on the ridiculously tall platform heels he was wearing. Rowena took his arm and lead him inside. 

“Well, let's at least have a look at you.” 

Sam clearly tried to pose, placing one hand on his hip and letting one side of his jacket slide off his shoulder to show off his dress more clearly. He was also obviously embarrassed, shyly unable to maintain eye contact and slouching. 

Rowena took it all in. His dress was a skintight satin in bright pink. It was in sharp contrast to the honeyed tan of his skin. The thin straps bit into his broad shoulders and led the eye down to low cut, well-structured cups meant to emphasize his breasts, if he'd had them. There were thin sheer panels from waist to hemline going over each hip bone in front, giving the allusion of a curvier body. The hem hugged the curve of his lower thigh just above the knee. In contrast, his shaggy fake fur coat was in electric lime green, long sleeved and came to just below his ass. There was black nail polish sloppily applied to his blunt finger nails. He had tried to do his makeup. The colors weren't far off and the lip gloss was fairly even, but the blush was applied a bit thick in bright spots over the apples of his cheeks and his eyeliner was thick and smudgy, obviously applied by an unpracticed, unsteady hand. 

And nothing was able to hide that at least one part of Sam was enjoying the attention. 

“So did you skin the Grinch on the way here, love?” Rowena asked teasingly. 

Sam took a step forward and barely caught himself from tumbling down. 

“You're about as steady as a new born giraffe in those things. Here, let's sit you down and get you out of those before you break that pretty neck of yours.” Rowena took his hand and guided him to a nearby chair. Sam sulked, but complied. 

She pulled up another chair and coaxed Sam into giving her one of his feet. Rowena carefully undid the shoe's strap, pulled it off, and tossed it aside. 

“Come on, give us the other one.” She tapped his leg until he switched feet. 

Rowena repeated her actions with his other foot, this time gently rubbing the instep of his foot. “There. Isn't that better?” 

Sam wiggled his toes and grumbled. Rowena could tell things were not going to plan, whatever that had been. 

“I see you shaved.” She slid her hand up a smooth leg. She looked him over a bit more. From what she could see, he'd been rather thorough. Rowena'd miss the chest hair, but she could work with this. “How was that?”

Sam broke out in a faint full body blush. “It was... nice,” he said softly, meeting her eyes for the first time.

“You look lovely.” Rowena looked around, hoping to find something to keep this going. “Do this often?”

“No,” Sam snorted.

“Just for me then? Well, what does a girl do to deserve something this special?” 

Sam shrugged. “This... was a bad idea.” He started to pull his foot back and stand up. 

Rowena still didn't have a clue what was going on, but it was far too interesting to let it go. “Wait! You're here, we have the place to ourselves, and I have bottle of Champagne that can make all bad ideas sound good again.” She smiled hopefully. 

“I don't know.” Sam was getting a bit twitchy.

“Look, you came all the way over here with no knickers on. There had to be a reason. You put a lot of work into... that. Let's not waste it. Would it help if I went and put on a tie?”

Sam snorted. “No.”

“I could fix your make up?”

“What's wrong with my make-up?” 

“Oh, dear. Nothing practice won't fix.” Rowena hesitated. “Let's go into the other room, paint each other's toenails, and see what kind of trouble that bottle of Champagne gets us into?” she tried again.

Sam covered his face with his hand for a moment. “I'm already here,” he grumbled and started to follow Rowena to the bedroom. He stopped. “No pictures.”

“Of course not,” she promised a bit too readily. 

“And not a word to Dean.”

“I wouldn't dream of it, dear.” Rowena excitedly nudged him back towards the bedroom. Her night finally got interesting.

**Author's Note:**

> Written for Winterfest in July Bingo 2019 at allbingo at Dreamwidth for the prompt "naughty."


End file.
